US5486598A - Silica mediated synthesis of peptides - Google Patents
Silica mediated synthesis of peptides Download PDFInfo
- Publication number
- US5486598A US5486598A US08/246,827 US24682794A US5486598A US 5486598 A US5486598 A US 5486598A US 24682794 A US24682794 A US 24682794A US 5486598 A US5486598 A US 5486598A
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- US
- United States
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- peptide
- reaction
- hse
- amino acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/123—Organometallic polymers, e.g. comprising C-Si bonds in the main chain or in subunits grafted to the main chain
- B01J31/124—Silicones or siloxanes or comprising such units
- B01J31/125—Cyclic siloxanes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- B01J37/036—Precipitation; Co-precipitation to form a gel or a cogel
Abstract
Description
TABLE 1 ______________________________________ Reaction Interactions* Steps (where and = no interaction) H.sub.f Kcal/mol ______________________________________ 1 D2 and A and G -933.4 0.0 2 A + H-bonded D2 and G -939.1 -5.7 3 A + D2 to S saddle and G -931.2 +2.2 4 AS Chain and G -945.7 -12.3 5 AS Chain + H-bonded G -953.5 -20.1 6 A + G + S Saddle -915.5 +17.9 7 AG Dipeptide + bonded S -941.8 -8.4 8 AG Dipeptide and S -934.6 -1.2 9 S to D2 Saddle and AG -933.4 0.0 10 Penta-coordinate D2 and AG -937.4 -4.0 11 Penta-coordinate Saddle and AG -929.4 +4.0 12 D2 + H-bonded H.sub.2 O and AG -932.2 +1.2 13 D2 and H.sub.2 O and AG Dipeptide -927.6 +5.8 ______________________________________ D2 = cyclotrisiloxane; A = alanine; G = glycine; S = trisiloxane chain; A = dipeptide
R--CH(NHA)--COOH
TABLE 2 __________________________________________________________________________ AMINO ACIDS # of Potential Bond Types Amino Acid Abbreviation Formula +Potential Bond Types 1 2 3 4 5 6 __________________________________________________________________________ Alanine ala ##STR1## 1 1 Arginine arg ##STR2## 1 2 1 Asparagine asn ##STR3## 1 2 1 Aspartic Acid asp ##STR4## 2 1 Cysteine cys ##STR5## 1 1 1 Glutamic Acid glu ##STR6## 2 1 Glutamine gln ##STR7## 1 2 1 Glycine gly ##STR8## 1 1 Histidine his ##STR9## 1 1 1 Isoleucine ile ##STR10## 1 1 Leucine leu ##STR11## 1 1 Lysine lys ##STR12## 1 2 Methionine met ##STR13## 1 1 Phenylalanine phe ##STR14## 1 1 Proline pro ##STR15## 1 Serine ser ##STR16## 1 1 Threonine thr ##STR17## 1 1 Tryptophan trp ##STR18## 1 1 Tyrosine tyr ##STR19## 1 1 Valine val ##STR20## 1 1 __________________________________________________________________________
TABLE 3 ______________________________________ Sample ID Description ______________________________________ G + S 2.52 gm glycine in 100 ml DIW + 3 gm sol-gel silica A + S 1.06 gm alanine in 100 ml DIW + 3 gm sol-gel silica A + G + S 2.52 gm glycine, 1.06 gm alanine in 100 ml DIW + 3 gm sol-gel silica S 3 gm sol-gel silica in DIW A Alanine Standard 1.07 gm in 200 ml DIW ______________________________________
TABLE 4 ______________________________________ (A + S) #1% #2% #3% Growth Ratio Weeks Area Area Area 2:3 ______________________________________ Alanine Standard 98.082 0.4159 1.503 0.28 2 98.671 0.169 1.047 0.16 9 98.664 0.243 1.028 0.24 13 98.564 0.285 1.151 0.25 14 98.523 0.303 1.173 0.26 14 98.668 0.269 1.062 0.25 ______________________________________
TABLE 5 ______________________________________ ((A + S) + S) #1% #2% #3% Growth Ratio Weeks Area Area Area 2:3 ______________________________________ 11 + 2 98.597 0.343 1.061 0.32 11 + 3 98.555 0.378 1.067 0.35 ______________________________________
Claims (18)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/246,827 US5486598A (en) | 1994-05-20 | 1994-05-20 | Silica mediated synthesis of peptides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/246,827 US5486598A (en) | 1994-05-20 | 1994-05-20 | Silica mediated synthesis of peptides |
Publications (1)
Publication Number | Publication Date |
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US5486598A true US5486598A (en) | 1996-01-23 |
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US08/246,827 Expired - Fee Related US5486598A (en) | 1994-05-20 | 1994-05-20 | Silica mediated synthesis of peptides |
Country Status (1)
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5977204A (en) * | 1997-04-11 | 1999-11-02 | Osteobiologics, Inc. | Biodegradable implant material comprising bioactive ceramic |
EP1006127A2 (en) * | 1998-12-03 | 2000-06-07 | Degussa-Hüls Aktiengesellschaft | Catalysts for enantioselective epoxidation of carbon-carbon double bonds |
US6441212B1 (en) * | 1996-07-12 | 2002-08-27 | Research Foundation Of State University Of New York | Silanol enzyme inhibitors |
US6495168B2 (en) | 2000-03-24 | 2002-12-17 | Ustherapeutics, Llc | Nutritional supplements formulated from bioactive materials |
US20050240281A1 (en) * | 1997-05-30 | 2005-10-27 | Slivka Michael A | Fiber-reinforced, porous, biodegradable implant device |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4280992A (en) * | 1978-02-14 | 1981-07-28 | Sanyo Chemical Industries, Ltd. | Immunologically active substance-glass conjugates, process for producing the same and diagnostic reagents containing the same |
JPS638390A (en) * | 1986-06-27 | 1988-01-14 | Lion Corp | Composition containing silicon compound |
JPS638389A (en) * | 1986-06-27 | 1988-01-14 | Lion Corp | Production of silicon compound |
US4927952A (en) * | 1987-05-26 | 1990-05-22 | Exsymol S.A.M. | Silanol condensation products |
US4985405A (en) * | 1987-02-06 | 1991-01-15 | Jean Gueyne | Therapeutic product based on organic silicon derivatives |
US5229096A (en) * | 1990-11-19 | 1993-07-20 | Scm Chemicals, Inc. | Silica gel |
-
1994
- 1994-05-20 US US08/246,827 patent/US5486598A/en not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4280992A (en) * | 1978-02-14 | 1981-07-28 | Sanyo Chemical Industries, Ltd. | Immunologically active substance-glass conjugates, process for producing the same and diagnostic reagents containing the same |
JPS638390A (en) * | 1986-06-27 | 1988-01-14 | Lion Corp | Composition containing silicon compound |
JPS638389A (en) * | 1986-06-27 | 1988-01-14 | Lion Corp | Production of silicon compound |
US4985405A (en) * | 1987-02-06 | 1991-01-15 | Jean Gueyne | Therapeutic product based on organic silicon derivatives |
US4927952A (en) * | 1987-05-26 | 1990-05-22 | Exsymol S.A.M. | Silanol condensation products |
US5229096A (en) * | 1990-11-19 | 1993-07-20 | Scm Chemicals, Inc. | Silica gel |
Non-Patent Citations (16)
Title |
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Bioceramics, vol. 5, "Reaction Kinetics of Bioactive Ceramics Part V: Molecular Orbital Modeling of Bioactive Glass Surface Reactions," West et al, pp. 75-86 (1992). |
Bioceramics, vol. 5, Reaction Kinetics of Bioactive Ceramics Part V: Molecular Orbital Modeling of Bioactive Glass Surface Reactions, West et al, pp. 75 86 (1992). * |
Biocermaics, vol. 6, "The Kinetics of Bioactive Ceramics Part VI: Silica-Water-Amino Acid Interactions," Hench et al, pp. 35-40 (1993). |
Biocermaics, vol. 6, The Kinetics of Bioactive Ceramics Part VI: Silica Water Amino Acid Interactions, Hench et al, pp. 35 40 (1993). * |
Chem. Rev., vol. 90, No. 1, "The Sol-Gel Process," Hench et al, pp. 33-72 (1990). |
Chem. Rev., vol. 90, No. 1, The Sol Gel Process, Hench et al, pp. 33 72 (1990). * |
J. Am. Ceram. Soc., vol. 74, No. 7, "Bioceramics: From Concept to Clinic," Hench, pp. 1487-1510 (1991). |
J. Am. Ceram. Soc., vol. 74, No. 7, Bioceramics: From Concept to Clinic, Hench, pp. 1487 1510 (1991). * |
Journal of Biomedical Materials Research, vol. 28, No. 5, "AM-1 molecular orbital calculations of silica-alanine-nitrogen interaction," West et al, pp. 625-633 (1994). |
Journal of Biomedical Materials Research, vol. 28, No. 5, AM 1 molecular orbital calculations of silica alanine nitrogen interaction, West et al, pp. 625 633 (1994). * |
Journal of Biomedical Materials Research, vol. 6, No. 5, "The Epitaxy of Poly-L-Alanine on L-Quartz and a Glass-Ceramic," Hartwig et al, pp. 413-474 (1972). |
Journal of Biomedical Materials Research, vol. 6, No. 5, The Epitaxy of Poly L Alanine on L Quartz and a Glass Ceramic, Hartwig et al, pp. 413 474 (1972). * |
Journal of Non Crystalline Solids, vol. 152, Interactions of water with trisiloxane rings. I. Experimental analysis, Wallace et al, pp. 101 108 (1993). * |
Journal of Non Crystalline Solids, vol. 152, Interactions of water with trisiloxane rings. II. Theoretical analysis, West et al, pp. 109 117 (1993). * |
Journal of Non-Crystalline Solids, vol. 152, "Interactions of water with trisiloxane rings. I. Experimental analysis," Wallace et al, pp. 101-108 (1993). |
Journal of Non-Crystalline Solids, vol. 152, "Interactions of water with trisiloxane rings. II. Theoretical analysis," West et al, pp. 109-117 (1993). |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6441212B1 (en) * | 1996-07-12 | 2002-08-27 | Research Foundation Of State University Of New York | Silanol enzyme inhibitors |
US5977204A (en) * | 1997-04-11 | 1999-11-02 | Osteobiologics, Inc. | Biodegradable implant material comprising bioactive ceramic |
US6344496B1 (en) | 1997-04-11 | 2002-02-05 | Osteobiologics, Inc. | Biodegradable implant material comprising bioactive ceramic |
US20050240281A1 (en) * | 1997-05-30 | 2005-10-27 | Slivka Michael A | Fiber-reinforced, porous, biodegradable implant device |
US7524335B2 (en) * | 1997-05-30 | 2009-04-28 | Smith & Nephew, Inc. | Fiber-reinforced, porous, biodegradable implant device |
EP1006127A2 (en) * | 1998-12-03 | 2000-06-07 | Degussa-Hüls Aktiengesellschaft | Catalysts for enantioselective epoxidation of carbon-carbon double bonds |
EP1006127A3 (en) * | 1998-12-03 | 2001-09-26 | Degussa AG | Catalysts for enantioselective epoxidation of carbon-carbon double bonds |
US6538105B1 (en) | 1998-12-03 | 2003-03-25 | Degussa Ag | Catalysts for the enantioselective epoxidation of C═C double bonds |
US6495168B2 (en) | 2000-03-24 | 2002-12-17 | Ustherapeutics, Llc | Nutritional supplements formulated from bioactive materials |
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Owner name: FLORIDA, UNIVERSITY OF, FLORIDA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:WEST, JON K.;HENCH, LARRY L.;REEL/FRAME:007018/0490 Effective date: 19940517 |
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